Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
  • C07C51/58—Preparation of carboxylic acid halides

Definitions

• This invention relates to the manufacture of isobutyryl flouride and more particularly pertains to a continuous process for the production of isobutyryl fluoride by the reaction of propylene, carbon monoxide and hydrogen fluoride.
• the present invention which relates to the production of isobutyryl fluoride is highly advantageous over the prior art processes for production of isobutyric acid or esters in that the former proceeds at a rapid rate and produces high yields (90% or greater) of the desired isobutyryl fluoride with a desirably low ratio of hydrogen fluoride to isobutyryl fluoride at the reactor outlet.
• reaction of propylene, carbon monoxide and hydrogen fluoride can be carried out under substantially anhydrous conditions continuously to produce high yields of isobutyryl fluoride in a relatively short period of time by conducting the reaction in a continuous flow of the reactants in more than one reaction zone, wherein additional carbon monoxide and propylene are added to the reaction mixture at a point or points between said reaction zones.
• Our process can be carried out at pressures varying between atmospheric and 2200 p.s.i.a. and preferably between 300 and 1000 p.s.i.a.
• the process of our invention can be carried out at temperatures in the range of from 0° C. to 100° C. and preferably between about 25° C. and 60° C.
• the total reaction time, or average residence time of the reaction mixture in the reactor, for converting 90% or more of the propylene fed in our process to isobutyryl fluoride can vary from 15 seconds to 10 minutes and usually from 30 seconds to 3 minutes.
• the molar ratio of propylene:carbon monoxide:hydrogen fluoride used as feed in our process can vary from 1:5:5 to 1:30:200, and more preferably from 1:7:15 to 1:20:100.
• Our process can be carried out in any continuous flow type of reactor which has at least two reaction zones which communicate and which have means between them for the introduction of additional portions of carbon monoxide and propylene.
• our process involves the addition of hydrogen fluoride, propylene and carbon monoxide to the first reaction zone with further additions of carbon monoxide and propylene only into the second and succeeding reaction zones.
• One type of reactor which can be used in the process of this invention is a pipe reactor having two or more tubular reaction zones within it, which zones communicate with one another and have means between them for the introduction of additional reactants into the direction of flow of the reaction mixture.
• reaction mixture produced by the process of our invention can be worked up by means known to those skilled in the art to isolate the desired isobutyryl fluoride in essentially pure form and to recycle unreacted carbon monoxide, propylene and hydrogen fluoride if so desired.
• Isobutyryl fluoride is readily converted to isobutyric acid by aqueous hydrolysis or it can be converted to an isobutyric acid ester by reaction with an alcohol as is well known in the art of hydrolysis or alcoholysis of acyl halides.
• Isobutyric acid and its esters have known uses, per se, and they can also be converted to methacrylic acid and methacrylic esters by oxydehydrogenation over a heterogeneous catalyst if desired as is also well known to those skilled in the art.
• the reactor was a tubular reactor of about 1/8" diameter and approximately 500 feet long. About midway along the reactor tube was an inlet for admitting additional feed to the reaction mixture, thus creating two reaction zones.
• the mixtures of HF/propylene/CO in which the CO/propylene molar ratio was about 13 and the HF/propylene molar/ratio was slightly over 40 was fed into one end of the reactor and was pumped continuously through the reactor at 525 p.s.i.g. at room temperature.
• a mixture of CO/propylene was introduced continuously into the inlet of the reactor at the midpoint.
• the reaction time was about 1-2 minutes. Analysis of the effluent from the reactor outlet at the end of the second reaction zone showed that the overall molar yield of isobutyryl fluoride (based on propylene fed) was 90%.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Glass Compositions (AREA)
• Saccharide Compounds (AREA)
• Investigating Or Analyzing Materials By The Use Of Ultrasonic Waves (AREA)
• Amplifiers (AREA)
• Ultra Sonic Daignosis Equipment (AREA)
• Meat, Egg Or Seafood Products (AREA)
• Medicines Containing Material From Animals Or Micro-Organisms (AREA)
• Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
• Catalysts (AREA)

Priority Applications (10)

Applications Claiming Priority (1)

Publications (1)

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ID=24007382

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Cited By (3)

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Citations (2)

Family Cites Families (4)

• 1983
  • 1983-06-15 US US06/504,702 patent/US4499029A/en not_active Expired - Fee Related
• 1984
  • 1984-04-03 DE DE8484103665T patent/DE3475399D1/de not_active Expired
  • 1984-04-03 EP EP84103665A patent/EP0131690B1/en not_active Expired
  • 1984-04-03 AT AT84103665T patent/ATE38978T1/de active
  • 1984-04-04 ES ES531267A patent/ES531267A0/es active Granted
  • 1984-04-19 CA CA000452411A patent/CA1234838A/en not_active Expired
  • 1984-06-06 JP JP59116334A patent/JPS608236A/ja active Pending
  • 1984-06-14 FI FI842431A patent/FI842431A/fi not_active Application Discontinuation
  • 1984-06-14 NO NO842386A patent/NO158377C/no unknown
  • 1984-06-14 PT PT78738A patent/PT78738B/pt unknown

Patent Citations (2)

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